ES2237184T3 - Deposicion catalizada de mensajeros potenciada. - Google Patents
Deposicion catalizada de mensajeros potenciada.Info
- Publication number
- ES2237184T3 ES2237184T3 ES99958831T ES99958831T ES2237184T3 ES 2237184 T3 ES2237184 T3 ES 2237184T3 ES 99958831 T ES99958831 T ES 99958831T ES 99958831 T ES99958831 T ES 99958831T ES 2237184 T3 ES2237184 T3 ES 2237184T3
- Authority
- ES
- Spain
- Prior art keywords
- inorganic salt
- cooh
- compound
- consisting essentially
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000008021 deposition Effects 0.000 title claims description 13
- 239000000758 substrate Substances 0.000 claims abstract description 40
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 20
- 102000003992 Peroxidases Human genes 0.000 claims abstract description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
- 229910017053 inorganic salt Inorganic materials 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 239000003623 enhancer Substances 0.000 claims description 30
- 235000002639 sodium chloride Nutrition 0.000 claims description 21
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 10
- 239000011780 sodium chloride Substances 0.000 claims description 8
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 6
- 239000001103 potassium chloride Substances 0.000 claims description 5
- 230000003321 amplification Effects 0.000 claims description 4
- 238000003199 nucleic acid amplification method Methods 0.000 claims description 4
- 108040007629 peroxidase activity proteins Proteins 0.000 claims description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005695 Ammonium acetate Substances 0.000 claims description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 229940043376 ammonium acetate Drugs 0.000 claims description 3
- 235000019257 ammonium acetate Nutrition 0.000 claims description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 3
- 239000001110 calcium chloride Substances 0.000 claims description 3
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 3
- 235000011148 calcium chloride Nutrition 0.000 claims description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 3
- 235000011147 magnesium chloride Nutrition 0.000 claims description 3
- 239000001488 sodium phosphate Substances 0.000 claims description 3
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 3
- -1 tyramine compound Chemical class 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 108010001336 Horseradish Peroxidase Proteins 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 230000002255 enzymatic effect Effects 0.000 claims 1
- 229960003732 tyramine Drugs 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 125000001626 borono group Chemical group [H]OB([*])O[H] 0.000 abstract 1
- 238000001514 detection method Methods 0.000 description 40
- 102100034763 Peroxiredoxin-2 Human genes 0.000 description 34
- 239000000047 product Substances 0.000 description 19
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 17
- 230000003647 oxidation Effects 0.000 description 17
- 238000007254 oxidation reaction Methods 0.000 description 17
- 101710185562 Peroxiredoxin 2 Proteins 0.000 description 15
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 13
- 238000000151 deposition Methods 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 230000027455 binding Effects 0.000 description 10
- 239000000872 buffer Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000012634 fragment Substances 0.000 description 8
- 239000007976 Tris-NaCl-Tween buffer Substances 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- STOOUUMSJPLRNI-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[[4-[4-[(4-hydroxyphenyl)diazenyl]phenyl]phenyl]diazenyl]-6-[(4-nitrophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=C(N=NC=3C=CC(=CC=3)C=3C=CC(=CC=3)N=NC=3C=CC(O)=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 STOOUUMSJPLRNI-UHFFFAOYSA-N 0.000 description 5
- SXEHKFHPFVVDIR-UHFFFAOYSA-N [4-(4-hydrazinylphenyl)phenyl]hydrazine Chemical compound C1=CC(NN)=CC=C1C1=CC=C(NN)C=C1 SXEHKFHPFVVDIR-UHFFFAOYSA-N 0.000 description 5
- 239000000427 antigen Substances 0.000 description 5
- 102000036639 antigens Human genes 0.000 description 5
- 108091007433 antigens Proteins 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 210000002307 prostate Anatomy 0.000 description 4
- 230000009870 specific binding Effects 0.000 description 4
- KGLPWQKSKUVKMJ-UHFFFAOYSA-N 2,3-dihydrophthalazine-1,4-dione Chemical compound C1=CC=C2C(=O)NNC(=O)C2=C1 KGLPWQKSKUVKMJ-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PHOLIFLKGONSGY-CSKARUKUSA-N (e)-(3-methyl-1,3-benzothiazol-2-ylidene)hydrazine Chemical compound C1=CC=C2S\C(=N\N)N(C)C2=C1 PHOLIFLKGONSGY-CSKARUKUSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- YRNWIFYIFSBPAU-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C(N(C)C)C=C1 YRNWIFYIFSBPAU-UHFFFAOYSA-N 0.000 description 2
- LVSPDZAGCBEQAV-UHFFFAOYSA-N 4-chloronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=C(Cl)C2=C1 LVSPDZAGCBEQAV-UHFFFAOYSA-N 0.000 description 2
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000147041 Guaiacum officinale Species 0.000 description 2
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940091561 guaiac Drugs 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
- 230000002163 immunogen Effects 0.000 description 2
- 239000012120 mounting media Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- PELJYVULHLKXFF-UHFFFAOYSA-N (4-iodophenyl)boronic acid Chemical compound OB(O)C1=CC=C(I)C=C1 PELJYVULHLKXFF-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- NEGFNJRAUMCZMY-UHFFFAOYSA-N 3-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(C(O)=O)=C1 NEGFNJRAUMCZMY-UHFFFAOYSA-N 0.000 description 1
- VZWXNOBHWODXCW-ZOBUZTSGSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-[2-(4-hydroxyphenyl)ethyl]pentanamide Chemical compound C1=CC(O)=CC=C1CCNC(=O)CCCC[C@H]1[C@H]2NC(=O)N[C@H]2CS1 VZWXNOBHWODXCW-ZOBUZTSGSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102000008394 Immunoglobulin Fragments Human genes 0.000 description 1
- 108010021625 Immunoglobulin Fragments Proteins 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 108700020962 Peroxidase Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 125000004057 biotinyl group Chemical group [H]N1C(=O)N([H])[C@]2([H])[C@@]([H])(SC([H])([H])[C@]12[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000007824 enzymatic assay Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229940014144 folate Drugs 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001744 histochemical effect Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
- C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
- C07C235/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Biotechnology (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Inert Electrodes (AREA)
- Carbon And Carbon Compounds (AREA)
- Reinforced Plastic Materials (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10765498P | 1998-11-09 | 1998-11-09 | |
| US107654P | 1998-11-09 | ||
| US434742 | 1999-11-05 | ||
| US09/434,742 US6372937B1 (en) | 1998-11-09 | 1999-11-05 | Enhanced catalyzed reporter deposition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2237184T3 true ES2237184T3 (es) | 2005-07-16 |
Family
ID=26805004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99958831T Expired - Lifetime ES2237184T3 (es) | 1998-11-09 | 1999-11-08 | Deposicion catalizada de mensajeros potenciada. |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6372937B1 (de) |
| EP (1) | EP1129214B1 (de) |
| AT (1) | ATE288497T1 (de) |
| AU (1) | AU768695B2 (de) |
| CA (1) | CA2351579C (de) |
| DE (1) | DE69923580T2 (de) |
| ES (1) | ES2237184T3 (de) |
| WO (1) | WO2000028077A1 (de) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9400034D0 (sv) * | 1994-01-06 | 1994-01-06 | Glycorex Ab | Laktosaminderivat |
| US6518036B1 (en) * | 1999-03-17 | 2003-02-11 | Nen Life Science Products, Inc. | Method of permanent fluorescent assay |
| JP2002280842A (ja) * | 2001-03-21 | 2002-09-27 | Hitachi Ltd | 電力増幅器モジュール |
| WO2002087530A1 (en) * | 2001-04-27 | 2002-11-07 | The General Hospital Corporation | Tyrosinase assay |
| US6617125B2 (en) * | 2001-06-29 | 2003-09-09 | Perkinelmer Life Sciences, Inc. | Compositions for enhanced catalyzed reporter deposition |
| US20090163375A1 (en) | 2003-09-09 | 2009-06-25 | Bowman Christopher N | Use of Photopolymerization for Amplification and Detection of a Molecular Recognition Event |
| US7354706B2 (en) * | 2003-09-09 | 2008-04-08 | The Regents Of The University Of Colorado, A Body Corporate | Use of photopolymerization for amplification and detection of a molecular recognition event |
| PL209602B1 (pl) | 2005-10-20 | 2011-09-30 | Inst Chemii Bioorg Pan | Sposób otrzymywania amidu kwasu 3-(4-hydroksyfenylo)propanowego |
| ES2624450T3 (es) | 2007-09-18 | 2017-07-14 | Dako Denmark A/S | Método rápido y sensible para la detección de dianas biológicas |
| US20090137405A1 (en) * | 2007-11-16 | 2009-05-28 | Christopher Bowman | Detection of nucleic acid biomarkers using polymerization-based amplification |
| EP2398908B1 (de) | 2009-02-19 | 2013-08-21 | Dako Denmark A/S | Verfahren und verbindungen zum nachweis molekularer ziele |
| CN104714007B (zh) * | 2009-10-20 | 2017-04-12 | 丹麦达科有限公司 | 单个靶实体的免疫化学检测 |
| AU2011274369A1 (en) | 2010-07-02 | 2012-12-06 | Ventana Medical Systems, Inc. | Hapten conjugates for target detection |
| SG190892A1 (en) | 2010-12-30 | 2013-07-31 | Ventana Med Syst Inc | Enhanced deposition of chromogens utilizing pyrimidine analogs |
| ES2678211T3 (es) | 2012-03-27 | 2018-08-09 | Ventana Medical Systems, Inc. | Conjugados de señalización y procedimientos de uso |
| CA2957783C (en) | 2014-10-02 | 2023-02-28 | Ventana Medical Systems, Inc. | Polymers and conjugates comprising the same |
| EP3371594A1 (de) | 2015-11-06 | 2018-09-12 | Ventana Medical Systems, Inc. | Repräsentative diagnose |
| CN111656179B (zh) | 2017-11-13 | 2023-11-03 | 豪夫迈·罗氏有限公司 | 用于使用表位电泳进行样品分析的装置 |
| CN112789684B (zh) | 2018-10-01 | 2025-05-09 | 文塔纳医疗系统公司 | 用于预测对pd-1轴导向疗法的应答的方法和系统 |
| WO2020074742A1 (en) | 2018-10-12 | 2020-04-16 | F. Hoffmann-La Roche Ag | Detection methods for epitachophoresis workflow automation |
| JP7441243B2 (ja) | 2019-05-14 | 2024-02-29 | エフ. ホフマン-ラ ロシュ アーゲー | 試料分析のための装置および方法 |
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|---|---|---|---|---|
| US4521511A (en) | 1982-09-22 | 1985-06-04 | Enzyme Technology Company | Catalyzed colorimetric and fluorometric substrates for peroxidase enzyme determinations |
| DE3463395D1 (en) | 1983-02-11 | 1987-06-04 | Nat Res Dev | Enhanced luminescent or luminometric assay |
| GB8420053D0 (en) | 1984-08-07 | 1984-09-12 | Secr Social Service Brit | Enhanced luminescent/luminometric assay |
| US4835101A (en) | 1986-02-10 | 1989-05-30 | Kallestad Diagnostics, Inc. | Luminescent analyses with enhanced storage stability |
| US5196306A (en) | 1989-03-29 | 1993-03-23 | E. I. Du Pont De Nemours And Company | Method for the detection or quantitation of an analyte using an analyte dependent enzyme activation system |
| US5629168A (en) | 1992-02-10 | 1997-05-13 | British Technology Group Limited | Chemiluminescent enhancers |
| US5688966A (en) | 1996-07-26 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Compounds and method for synthesizing sulfoindocyanine dyes |
| US5863748A (en) | 1997-03-14 | 1999-01-26 | New Life Science Products, Inc. | p-Hydroxycinnamoyl-containing substrates for an analyte dependent enzyme activation system |
| US6518036B1 (en) * | 1999-03-17 | 2003-02-11 | Nen Life Science Products, Inc. | Method of permanent fluorescent assay |
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1999
- 1999-11-05 US US09/434,742 patent/US6372937B1/en not_active Expired - Lifetime
- 1999-11-08 WO PCT/US1999/026327 patent/WO2000028077A1/en not_active Ceased
- 1999-11-08 CA CA002351579A patent/CA2351579C/en not_active Expired - Lifetime
- 1999-11-08 EP EP99958831A patent/EP1129214B1/de not_active Expired - Lifetime
- 1999-11-08 ES ES99958831T patent/ES2237184T3/es not_active Expired - Lifetime
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- 1999-11-08 DE DE69923580T patent/DE69923580T2/de not_active Expired - Lifetime
- 1999-11-08 AT AT99958831T patent/ATE288497T1/de not_active IP Right Cessation
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2001
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| EP1129214A1 (de) | 2001-09-05 |
| CA2351579C (en) | 2010-01-19 |
| EP1129214B1 (de) | 2005-02-02 |
| US6372937B1 (en) | 2002-04-16 |
| WO2000028077A1 (en) | 2000-05-18 |
| US6593100B2 (en) | 2003-07-15 |
| DE69923580D1 (de) | 2005-03-10 |
| CA2351579A1 (en) | 2000-05-18 |
| AU768695B2 (en) | 2004-01-08 |
| DE69923580T2 (de) | 2006-01-05 |
| ATE288497T1 (de) | 2005-02-15 |
| US20010039035A1 (en) | 2001-11-08 |
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